Wanted: The most interesting problem in B2B Sales

Why?

LLMs can now address nearly every problem in business processes – provided someone at your company is willing to go through the pain of implementing the system, and is given permission to do so. If you're both at the same time, congratulations – nice to be talking to peers.

I'm on a quest to identify the most interesting problem by talking to practitioners.

I've spent the last decade working at the intersection of B2B sales, revenue operations, and growth, and built AI systems (initially running under the boring name "machine learning") all throughout – the kind that cut one team's call prep from 15+ minutes to 30 seconds. I've had the pleasure of talking to well over 400 people from that field – mostly about their problems.

One pattern resurfaced again and again: Even when the ingredients of B2B sales look straightforward, the full orchestration is hard, because the parts are multiplicative, not additive – each one depends on the others.

Theory of constraints is the lens I reach for: map the revenue engine, find the real constraint, weigh the effort to solve it, then start with the best effort-to-impact ratio. Easy to say, hard to do – the loudest pain is rarely the binding constraint, so most of us (me included) end up working the noise.

That gap is why I'm writing this. The problem I'm after is the genuinely hard one hiding behind the obvious one.

What interesting means to me

Simply put: Something that needs a maker schedule to solve well.

I'm looking for a hard problem. Lots of data – the kind that doesn't fit in an LLM's context window and that's going to send your LLM bill through the roof. Things that might require a graph. Building systems. Requires frameworks to solve.

What isn't fully solved:

Trust: Both internal and external.
Next actions: Every sales rep knowing exactly what to do next.
Networks: How you find and act on the relationships between entities (people, companies, …).
Forecasting: Deals and revenue – largely solves itself once everything upstream is addressed.
Control: Knowing whether the work is actually getting done – not just what the CRM says – and being able to act on it.
... Your specific problem I hadn't thought of while writing this.

What I don't find interesting

Things that are already fully solved – TOFU / acquisition, generic data integration, automatically routing feedback to the product team.

If someone on your team could address all your challenges between three meetings, this isn't for me.

Building AI agents or skills as the deliverable. Navigating internal politics. Consulting, getting hired, working on a time-based contract.

Selection mechanism

I'm constraining this to keep myself accountable and to make how I'll decide clear to everyone involved from the start:

I'll have first conversations with at least 19 people (37% of a 51-conversation cap – see Secretary problem).
The first 19 calibrate the bar.
After that, the first conversation that beats every prior one stops the search.
I'll then talk to up to 4 finalists in depth.
Pick 1 to collaborate with – or none.
Work on the problem until it's solved.
Willing to go to 51 first conversations if nobody clears the bar.
Until I've picked someone, this is my main thing. After that, I'm in the work and out of conversation mode again.

Constraints

You're not looking for help with lead generation. If that's where you're struggling I'm happy to connect you with partners that are exceptional at that.
Attio or HubSpot CRM.
Existing sales motion.

Unless you can make the decision all on your own, I'll want a thorough conversation with the economic buyer before we commit.

Bonus

Your company is a B Corp.

Who is writing this

In case we never spoke before – or you want a refresher:

Founded a software company in the B2B sales space – raised a €750k pre-seed and shipped agentic systems before "agentic" was a marketing term. Pivoted multiple times; each time, had to build pipeline from zero. The product worked well, but the founders had different priorities.
Moved on to working solo. Worked with a handful of clients on hard problems – helped 4× closed revenue in four months and lifted outbound reply rates from ~10% to over 30% through fully automated lead scoring and personalization.
Worked as Head of Growth & Head of Sales.
Consulted more than a dozen B2B revenue teams on strategy, processes, and tooling.
No longer interested in solving large problems at scale.
Want to work on things that are stimulating.

How I work

The retainer model is dead; it sets the wrong incentives.

I work on a success-only basis. I price for outcome, not time. The number reflects the size of the problem; the guarantee reflects my conviction.

Payment is tied to clearly defined milestones. The number will be substantial – and so will the return on it. Neither of us should waste time on work that doesn't shift the needle.

We define upfront:

The business case
Milestones
A mutual action plan
Success criteria
Guarantee

The guarantee is simple: I work the problem until it's done.